Lessons From a Couple of Entrepreneurial Power Couples


I have had the privilege of interviewing hundreds of successful leaders, but not many have been married to one another. A couple of exceptions: two entrepreneurial power couples, Austin and Angela Allison and Chris and Heidi Powell.

Originally from Cincinnati Ohio, Austin and Angela Allison disrupted the real estate market with the introduction of their first company dotloop. dotloop eliminated paper transactions turning what is often a headache into a seamless digital process. The acquisition of dotloop by Zillow Group moved the couple to San Francisco where they quickly fell in love with wine culture. Realizing a gap in the wine industry for premium quality at an approachable price point, the Allisons created WineSociety.

Launched in January 2018, WineSociety is a premium wine subscription company that is on a mission to change the way Americans purchase and consume wine. Modernizing delivery for today's lifestyle, WineSociety arrives directly to your doorstep in its trademark 500mL cans (perfect amount for sharing), ready to accompany you on any adventure. Single flavor and variety pack monthly subscriptions are available on winesociety.com. WineSociety is simplifying the process of making wine accessible, convenient and affordable to everyone.

Chris and Heidi Powell are perhaps best known as the former co-hosts of ABC's Extreme Weight Loss. With an unyielding dedication to helping others, Chris started as the original host of the show, traveling the country using his innovative techniques, education and expertise to guide extremely overweight individuals as they shed hundreds of pounds over the course of a year. Heidi authors an incredibly successful blog (www.heidipowell.net) where she shares her insight and expertise on health and wellness trends, fitness regimens, healthy recipes, marriage and parenting advice, and her secrets to balancing it all. Heidi is beloved for her candid and vulnerable voice, which connects with more than 4 million women, mothers, and fitness experts worldwide. The Powells created their comprehensive fitness app TRANSFORM, which relaunched with their 2.0 version this past November and is designed to take people from the foundational steps of wellness change to a complete redesign of their body and life.

Here are some are excerpts from my interviews with Austin and Angela Allison and Chris and Heidi Powell

Adam: How did you get here? What failures, setbacks or challenges have been most instrumental to your growth?

Angela: In 2012, Austin’s company dotloop brought us to California and we began our split lifestyle between Cincinnati, OH and San Francisco, CA. Being from the midwest, we didn’t drink wine. It was a little foreign to us, seemed out of reach, expensive and just intimidating. However, now living only an hour away from wine country, and hearing amazing things about it, we set our preconceived notions aside and planned our first trip to Napa Valley. We were shocked at how inviting and welcoming the culture was and couldn’t believe we had been missing out for so long! Over the years, we continued to grow our appreciation for Napa Valley and wine in general and began to share that experience with friends. Having the opportunity to compare the difference in cultural uniqueness, product offerings, and personal habits between the midwest and California got our minds turning. There was still a barrier and intimidation that existed for many (as we had experienced) and we saw an opportunity to start a company, where we bring great quality wine in simple familiar packaging (cans) without all the complexity and at an affordable price. A drinkable everyday wine.

The biggest hurdle we’ve faced is the industry’s archaic methods. The alcohol industry hasn’t progressed far past the prohibition days. It can take months for shipping approval to any one state! Following approval, the process from purchase to delivery involves at least 5 third-party companies or systems. But that is one of the things that intrigued us about this industry. It is similar to how the real estate industry was when we started dotloop. 

The biggest challenge as executive leaders has been to learn to follow our own instincts. It is so important to be a good listener and be open to opinions and advice, but it is also important to know when to take action and follow your gut instinct. A few times since the launch we have made the mistake of doing what others thought we should do, instead of doing what we originally planned and ended up having to backtrack. One of WineSociety’s core company values, is “Fail Forward”. Mistakes will always be made, but you can use them as an opportunity to grow..

Adam: What is something about you that many people who follow you don’t know? 

Heidi: That’s a tough question, because I think I might actually err on the side “over sharing” on social media! But one thing many people that follow me might not realize is that I love the business side of what we do. I was born into a family of businessmen with three brothers who toughened me up and taught me the ropes. It’s in my blood, and I love pairing the fast-paced, yet methodical, strategy with our passions!

Chris: I never intended to be a personal trainer and coach. While I have always been passionate about fitness, I actually planned to be an airline pilot. I got my private pilot’s license when I was 17, then went on to receive my commercial, instrument, multi-engine, and instructor ratings while I was attending college. I actually had an airline interview scheduled for Sept 13, 2001 – which, needless to say didn’t happen. Shortly after, I decided to give up on flying and pursue my passion – fitness. It all worked out pretty well!

Adam: Who are the best leaders you have been around and what have you learned from them? What do you believe everyone should know about leadership? 

Chris: In our years, we have worked with a LOT of bosses and a few leaders. No single leader comes to mind that truly stands out, but we have learned some very important characteristics that we choose to take from the few. 

There are bosses and there are leaders. Bosses tell others what to do, and typically operate through fear, using the constant threat of being replaced. Leaders will jump into the trenches to work WITH YOU, challenging you to take on greater responsibility until you have the skill and experience to handle the job on your own. They use positive reinforcement, accountability, and regular reporting to gauge your performance. Leaders are fair, communicate clearly and authentically, and seek to understand all perspectives when making difficult decisions. 

Heidi: As crazy as it sounds, the best leaders I know are people that actually work FOR me and Chris. We have some of the best employees and partners, and I’ve been lucky to have a few really great ones that have lead their teams or departments like champs. And believe it or not, my assistant has some of the best qualities I like to see in a leader. She’s compassionate and will never speak an ill word about anyone, she takes responsibility when she messes up, and works harder than anyone I’ve ever seen. 

A few more leaders: BK Boreyko is the most generous CEO I’ve ever met. I love this man! My Grandpa, who is the most generous and unconditionally loving business owner on earth. Finally, Chris. I mean, I can’t think of a leader that can successfully enroll more people in a mission to change the world. Not only does he get them on board, but he empowers them all to believe in themselves and their ability to achieve anything they set their minds to. One thing everyone should know about being a leader is that the best ones listen far more than they talk. They understand far deeper than they seek to be understood.

Adam: In your experience, what are the defining qualities of an effective leader? How can leaders and aspiring leaders take their leadership skills to the next level?

Austin: Listening, delegating and executing. Knowing when to listen and brainstorm and knowing when to execute. It is so easy to create ideations, but you will find yourself spinning in circles if you don’t set parameters and know when to execute. 

Another important quality is learning not to spend your time micromanaging. It is important to hire a team that you trust, and allow the team to grow together. Listening to opinions and knowing when to step in and make hard choices are key to a well oiled machine! 

The full interviews can be found at https://thriveglobal.com/stories/tips-from-the-top-conversation-with-austin-and-angela-allison/ and https://thriveglobal.com/stories/inside-influence-conversation-with-chris-and-heidi-powell/

Adam Mendler